US3234239A - Dibenzostannole compounds - Google Patents
Dibenzostannole compounds Download PDFInfo
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- US3234239A US3234239A US34625A US3462560A US3234239A US 3234239 A US3234239 A US 3234239A US 34625 A US34625 A US 34625A US 3462560 A US3462560 A US 3462560A US 3234239 A US3234239 A US 3234239A
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- dibenzostannole
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- 150000001875 compounds Chemical class 0.000 title description 33
- -1 STANNOLE COMPOUND Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DRKHIWKXLZCAKP-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)benzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1Br DRKHIWKXLZCAKP-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241001161813 Aponogeton junceus Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000532642 Conotrachelus nenuphar Species 0.000 description 1
- 241000252210 Cyprinidae Species 0.000 description 1
- 241000238578 Daphnia Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241000305186 Persectania ewingii Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 235000015926 Proboscidea louisianica ssp. fragrans Nutrition 0.000 description 1
- 235000015925 Proboscidea louisianica subsp. louisianica Nutrition 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 241000254112 Tribolium confusum Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 1
- LWHKXKZPLXYXRO-UHFFFAOYSA-L dichloro-bis(ethenyl)stannane Chemical class C=C[Sn](Cl)(Cl)C=C LWHKXKZPLXYXRO-UHFFFAOYSA-L 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Definitions
- substituents R and R may be vinyl groups and alkyl and aryl groups directly connected to the metallic atom; and where R and R" can be aikyl, aryl, methoxyl, dimethylamino, hydroxyl, amino or any groups that would not interfere with ring formation.
- the process of preparation involves reacting a diphenyl compound, for example, 2,2-dibromodiphenyl with butyl lithium (or an alkyl lithium) and a solution of an alkyl tin dihalide or appropriate organo tin halide to produce the compound desired, which compound precipitates from solution and, thereafter, is purified by washing and recrystallization.
- a diphenyl compound for example, 2,2-dibromodiphenyl with butyl lithium (or an alkyl lithium) and a solution of an alkyl tin dihalide or appropriate organo tin halide
- Example I he preparation of 1,1-dimethyl-2,3,4,5-dibenzostannole 2,2'-dibromodiphenyl (4 grams) was dissolved in ether (40 milliliters; anhydrous) and to the stirred solution there was added butyl lithium (2 equivalent :0.93N solution) in petrol ether (30 milliliters) during 8 minutes, and the temperature throughout the reaction being maintained at l. The mixture was stirred'for 4 hours at room temperature, during which period the solution became opaque and pale yellow in color. Finally the solution was refluxed for 0.5 hour. Refiuxing was continued and a solution of dimethyl tin dichloride (2.83 grams) in dry ether (40 milliliters) was added slowly during 18 minutes. The turbid solution flocculated initially, then as the latter addition was continued, a sticky solid was deposited. Additional ether milliliters) was added and the solution was stirred and refluxed for 2 hours.
- the dilithio compound is reactable with virtually any tin organic dihalide wherein the two halogen atoms react with the dilithiodiphenyl compound to attach themselves thereto and to give the substituted dibenzostannole thus dimethyl, diethyl, dipropyl, dibutyl, dipentyl, diphenyl and divinyl tin chlorides can be used as reactants with an appropriate o,o.'-'dilithiodiphenyl compound. Likewise other positions on two phenyl rings of the diphenyl compound can be occupied with a variety of substituent groups.
- the positions which are meta, para, and ortho, respectively, with respect to the junction point of the two phenyl groups in the formation of the diphenyl compound may be occupied by any of the alkyl, aryl, etc. groups which canbe introduced to those positions without materially allecting the steric properties of the compound.
- Example 11 Using the same procedure, but starting with 2,2'-dibromodiphenyloxide, the corresponding tin compound is formed. Likewise, the .diphenyl sulfide, sulfite, phosphide or selenide may be used.
- the Z may be entirely absent and the two phenyl rings joined directly at the indicated point, in which case the starting compound is a diphenyl; or the Z maybe oxygen, sulfur, sulfonyl, sulfite, and nitrogen group as well as selenium, phosphorus or other organic radical or atom which is not affected by alkyl lithium.
- an o,o'-di Grignard compound can function in place of the dilithio compounds.
- R SnX in which the R-alkyl group may be any of the alkyl, aryl, aralkyl heterocyclic, alkoxy and virtually any organic substituent, because the reactive portion of this molecule is the halogen which is aimed at the alkali metal in the diphenyl compound.
- reaction conditions In conducting the reaction, due heed must be paid to the fundamental properties of the compounds and in general, relatively mild reaction conditions may be used. That is, temperatures from ambient or about 40 C. to temperatures as low as 80 C. are useful. Virtually any solvent which will hold reactant materials in solution is useful; typical useful solvents are tetrahydrofuranand dibutyl ether. Time of reaction and pressure on the reaction vessel, of course, are not critical variables. In general, since the reaction calls for mol for mol quantities, the reactants are most effective when handled in those quantities.
- the materials are organo metallic compounds of a special class, and as such find particular value'as temperature stabilizers and the like in organic fluid compositions, I have found that the compounds are also quite useful as insecticides. Preliminary tests show that the compounds in quite low concentrations will give a 100 percent kill for southern armyworm, bean aphid, two- 1 spotted spider mite, house fly, American cockroach, confused flour beetle, Daphnia, ramshorn snail, northern fatheaded minnows and plum curculio.
- the compounds are also useful as stabilizers in plastic compositions such as polyvinyl chloride, and for compositions such as insulating oils and transformer oils.
- the method of synthesis involves the preparation of the di-phenyl or di-aromatic compound with the ortho substituted lithium thus orienting the lithium so that it is reactable with the halide to give the final compound.
- the nature of the final compound desired will tell the chemist operator which reactants to use.
- R and R are independently selected from the group consisting of lower molecular weight alkyl, phenyl, alkylpheny-l, heterocyclic and alkoxy moieties and R" and R are independently selected from thegroup-consisting of alkyl, alkoxy, and substituted alkyl and alkoxy groups, said R, R, and R" groups in the alkyl and heterocyclic portions individually'carrying no more than about 6 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
United States Patent 3,234,239 DiBENZOSTANNOLE COMPOUNDS Francis Johnson, West Newton, Mass, assignor to The Dow Chemical Company, Midiand,--Mich., a corporation of Delaware No Drawing. Filed June 8, 1960, Ser. No. 34,625 8 Claims. --(Ci. 260-329) This invention relates to the preparation of new tin heterocyclic compounds which may be basically characterized as dibenzostannole compounds and to the method for their preparation.
Organo metallic compounds of a variety of structures have been reported and have found an equally varied field of application. In general, they are useful for their thermal stability and related properties. Gilman and Gorsich, J.A.C.S., 77, 6380 (1955), have reported dibenzosilole compounds. Kuivila and Beurnel, J-.A.C.S., 80, 3250 (1959), have made and reported 'dibenzostannepin compounds.
It is a basic object of this invention to provide a simple, convenient, rather generalized method of preparing dienzostannole type compounds wherein reasonable variations in the structure of the compounds can be worked outin the process of synthesis.
The invention, accordingly, is embodied in a new class of compounds which may be generally characterized as having formulas corresponding to the specific formula derivable by reference to the following:
wherein the substituents R and R may be vinyl groups and alkyl and aryl groups directly connected to the metallic atom; and where R and R" can be aikyl, aryl, methoxyl, dimethylamino, hydroxyl, amino or any groups that would not interfere with ring formation.
The process of preparation involves reacting a diphenyl compound, for example, 2,2-dibromodiphenyl with butyl lithium (or an alkyl lithium) and a solution of an alkyl tin dihalide or appropriate organo tin halide to produce the compound desired, which compound precipitates from solution and, thereafter, is purified by washing and recrystallization.
The details of the process and the nature of the compound will be better understood by reference to the following specific example illustrating the synthesis:
Example I.-T he preparation of 1,1-dimethyl-2,3,4,5-dibenzostannole 2,2'-dibromodiphenyl (4 grams) was dissolved in ether (40 milliliters; anhydrous) and to the stirred solution there was added butyl lithium (2 equivalent :0.93N solution) in petrol ether (30 milliliters) during 8 minutes, and the temperature throughout the reaction being maintained at l. The mixture was stirred'for 4 hours at room temperature, during which period the solution became opaque and pale yellow in color. Finally the solution was refluxed for 0.5 hour. Refiuxing was continued and a solution of dimethyl tin dichloride (2.83 grams) in dry ether (40 milliliters) was added slowly during 18 minutes. The turbid solution flocculated initially, then as the latter addition was continued, a sticky solid was deposited. Additional ether milliliters) was added and the solution was stirred and refluxed for 2 hours.
Distilled water (25 milliliters) was added and the organic phase was separated from the aqueous layer. The
former was washed with water and set aside. The aqueous layer and washings were combined and'extracted with ether (2 x 20 milliliters). This extract was washed once with water (20 milliliters) and the ether extracts then combined and dried over anhydrous sodium sulfate. The ether was removed by distillation at normal pressure and residual organic solvents (butyl bromide and petrol ether) were removed, using a Water aspirator. The residue was a pale yellow sticky material containing a highly crystalline solid. It was dissolved in hot ethanol (approximately 18 milliliters) boiled with charcoal for a few minutes and then filtered. 'After concentrating this solution to 12 milliliters, it was allowed to cool slowly to room temperature. Long prismatic rods were deposited. When crystallization was complete, the solid (1.63 grams) was removed by filtration and washed with a little cold ethanol, then dried by air suction, MJP/ 119-122". One additional crystallization from ethanol gave the pure material as long thick needles, M.P. 123 124". [Found: C, 55.9; 'H, 418. C H Sn requires: C, 55.89; H, 4.69 percent] It will be apparent from an inspection of the method of synthesis and the formula of the family of compounds as given above that appropriate selection of substituted starting materials will give the correspondingly substituted dibenzostannole end product. For example, after converting the dihromodiphenyl to the corresponding dimethyl compound, the dilithio compound is reactable with virtually any tin organic dihalide wherein the two halogen atoms react with the dilithiodiphenyl compound to attach themselves thereto and to give the substituted dibenzostannole thus dimethyl, diethyl, dipropyl, dibutyl, dipentyl, diphenyl and divinyl tin chlorides can be used as reactants with an appropriate o,o.'-'dilithiodiphenyl compound. Likewise other positions on two phenyl rings of the diphenyl compound can be occupied with a variety of substituent groups. That is, the positions which are meta, para, and ortho, respectively, with respect to the junction point of the two phenyl groups in the formation of the diphenyl compound, may be occupied by any of the alkyl, aryl, etc. groups which canbe introduced to those positions without materially allecting the steric properties of the compound.
Example 11 Using the same procedure, but starting with 2,2'-dibromodiphenyloxide, the corresponding tin compound is formed. Likewise, the .diphenyl sulfide, sulfite, phosphide or selenide may be used.
Further, with respect to the variants of the diphenyl structure, the formula therefore :may be generalized as follows:
wherein the Z may be entirely absent and the two phenyl rings joined directly at the indicated point, in which case the starting compound is a diphenyl; or the Z maybe oxygen, sulfur, sulfonyl, sulfite, and nitrogen group as well as selenium, phosphorus or other organic radical or atom which is not affected by alkyl lithium.
With respect to the further generalization of the metal compound reactant therewith, it may he noted that an o,o'-di Grignard compound can function in place of the dilithio compounds. As the metal halide raw material alkyl tin dichloride, R SnX in which the R-alkyl group may be any of the alkyl, aryl, aralkyl heterocyclic, alkoxy and virtually any organic substituent, because the reactive portion of this molecule is the halogen which is aimed at the alkali metal in the diphenyl compound.
Employing the same method and selecting the tin halide reactant in accordance with the substituent organo group desired on tin in the ultimate compound, the following compounds are prepared:
In conducting the reaction, due heed must be paid to the fundamental properties of the compounds and in general, relatively mild reaction conditions may be used. That is, temperatures from ambient or about 40 C. to temperatures as low as 80 C. are useful. Virtually any solvent which will hold reactant materials in solution is useful; typical useful solvents are tetrahydrofuranand dibutyl ether. Time of reaction and pressure on the reaction vessel, of course, are not critical variables. In general, since the reaction calls for mol for mol quantities, the reactants are most effective when handled in those quantities.
I have found in general that the reaction proceeds rather easily at temperatures up to 40 or 50' C. and that yields of the order of 45 percent are readily obtainable.
Although the materials are organo metallic compounds of a special class, and as such find particular value'as temperature stabilizers and the like in organic fluid compositions, I have found that the compounds are also quite useful as insecticides. Preliminary tests show that the compounds in quite low concentrations will give a 100 percent kill for southern armyworm, bean aphid, two- 1 spotted spider mite, house fly, American cockroach, confused flour beetle, Daphnia, ramshorn snail, northern fatheaded minnows and plum curculio. The compounds are also useful as stabilizers in plastic compositions such as polyvinyl chloride, and for compositions such as insulating oils and transformer oils.
\ i:\ \CGHS It should be noted that the method of synthesis involves the preparation of the di-phenyl or di-aromatic compound with the ortho substituted lithium thus orienting the lithium so that it is reactable with the halide to give the final compound. The nature of the final compound desired will tell the chemist operator which reactants to use.
C l (DI/ What is claimed is: a 1. A stannole compound having a formula given by the following:
Sn R R wherein R and R are independently selected from the group consisting of lower molecular weight alkyl, phenyl, alkylpheny-l, heterocyclic and alkoxy moieties and R" and R are independently selected from thegroup-consisting of alkyl, alkoxy, and substituted alkyl and alkoxy groups, said R, R, and R" groups in the alkyl and heterocyclic portions individually'carrying no more than about 6 carbon atoms.
2. A compound corresponding to the following formula:
CH3 CH 3. A compound corresponding to the following formula:
CH CH 0H=OH,
4. A compound corresponding to the following formula:
i:\ O B505 @5115 5. A compound corresponding to the following formula:
5 6 6. A compound corresponding to the following References Cited by the Examiner formula: UNITED STATES PATENTS 2,980,633 4/1961 Koehler et a1 260-4297 5 3,079,414 2/1963 Tamborski et al. 260-429.7 OTHER REFERENCES czHso/ \oczm Ciilman et al., Journal of the American Chemical Society, vol. 77, No. 23, Dec. 5, 1955, pp. 6380-6381 7. A compound corresponding to the following relied 01L Gilrnan et a1., J.A.C.S,, 79 (Dec. 5, 1957 pp. 6339- 3 Henry et al., Journal of the American Chemical Society, vol. 82, No. 3, Feb. 5, 1960, pp. 561-563 relied on, 15 Hitchcock et al., J. Chem. Soc. (London), 1957, pp.
S11 4537-4546. CH3 CH3 Kuivila et al., Journal of the American Chemical 8. A compound corresponding to the following Society, vol. 80, No. 13, July 1958, pp. 3250-3253 relied formula: on.
20 Oita et al., J.A,C.S., 79 (January 1957), pp. 339-342. @1130 00113 Patterson et 211., The Ring Index," Reinhold Publishing Corp., 1940, pp. 248 and 249 relied on. S TOBIAS E. LEVOW, Primary Examiner.
CH3 25 ABRAHAM H. WINKELSTEIN, Examiner.
Claims (1)
1. A STANNOLE COMPOUND HAVING A FORMULA GIVEN BY THE FOLLOWING
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34625A US3234239A (en) | 1960-06-08 | 1960-06-08 | Dibenzostannole compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34625A US3234239A (en) | 1960-06-08 | 1960-06-08 | Dibenzostannole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3234239A true US3234239A (en) | 1966-02-08 |
Family
ID=21877571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US34625A Expired - Lifetime US3234239A (en) | 1960-06-08 | 1960-06-08 | Dibenzostannole compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3234239A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502616A (en) * | 1966-09-20 | 1970-03-24 | Christian H Stapfer | Organotin sulfide stabilizer composition and polymers stabilized therewith |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2980633A (en) * | 1957-03-05 | 1961-04-18 | Union Carbide Corp | Carbon and graphite articles |
| US3079414A (en) * | 1959-09-18 | 1963-02-26 | Tamborski Christ | Method of preparing heterocyclic compounds containing metals or metalloids |
-
1960
- 1960-06-08 US US34625A patent/US3234239A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2980633A (en) * | 1957-03-05 | 1961-04-18 | Union Carbide Corp | Carbon and graphite articles |
| US3079414A (en) * | 1959-09-18 | 1963-02-26 | Tamborski Christ | Method of preparing heterocyclic compounds containing metals or metalloids |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502616A (en) * | 1966-09-20 | 1970-03-24 | Christian H Stapfer | Organotin sulfide stabilizer composition and polymers stabilized therewith |
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